Method for producing MPS-compatible water gradient contact lenses
The invention is related to a process for producing contact lenses that not only comprise a water gradient structural configurations, but also have a minimized uptakes of polyquaternium-1 and a long-lasting surface hydrophilicity and wettability even after being undergone a 30-days lens care regime.
1. A process for producing contact lenses, comprising the steps of:
(a) obtaining a contact lens precursor which is a coated contact lens and has a first polyquaternium-1 uptake (“PU o ”), wherein the coated contact lens comprises a lens bulk material completely covered with an anchor layer of a polyanionic polymer and an outer surface hydrogel layer covalently attached to the anchor layer, wherein the polyanionic polymer comprises at least 60% by mole of repeating units of at least one carboxyl-containing vinylic monomer; and
(b) heating the contact lens precursor in an aqueous solution in the presence of at least one polyaziridine to and at a temperature from about 30° C. to about 140° C. for a period of time sufficient to obtain the contact lens having a second polyquaternium-1 uptake (“PU pz ”), wherein the polyaziridine having a number average molecular weight of about 2000 Dalton or less and at least two aziridine groups each of which is a mono-valent radical of formula
in which R1 is hydrogen, methyl or ethyl, wherein (PU o -PU pz )/PU o is at least 60%.
2. The process of claim 1 , wherein said at least one polyaziridine is selected from a group consisting of trimethylolpropane tris(2-methyl-1-aziridinepropionate), pentaerythritol tris[3-(1-aziridinyl)propionate], trimethylolpropane tris(3-aziridinopropionate), a Michael reaction product of a vinylic crosslinker having at least three (meth)acryloyl groups and 2-methylaziridine, a Michael reaction product of a vinylic crosslinker having at least three (meth)acryloyl groups and aziridine, or a combination thereof.
3. The process of claim 2 , wherein the aqueous solution comprises two polyaziridines, a first polyaziridine having at least two aziridine groups of
and a second polyaziridine having at least two aziridine groups of
and at least one hydrophilic moiety selected from the group consisting of —OH, —[OC 2 H 4 O] n1 —, —CONHR 1 , —CONR 1 —, and combinations thereof, wherein n1 is an integer of 1 to 10 and R 1 is hydrogen, methyl or ethyl.
4. The process of claim 3 , wherein the aqueous solution comprises from about 0.01% to about 2.5% by weight of said at least one polyaziridine.
5. The process of claim 4 , wherein the aqueous solution is a lens packaging solution, wherein the step of heating is performed by autoclaving the contact lens precursor immersed in the lens packaging solution in a sealed lens package at a temperature of from about 115° C. to about 125° C. for approximately 20-90 minutes.
6. The process of claim 5 , wherein the lens packaging solution further comprises a partially hydrolyzed polyvinyl alcohol having a hydrolysis degree of hydrolysis of from about 80% to about 98%.
7. The process of claim 5 , wherein the lens packaging solution has a pH of from about 7.0 to about 9.0 before autoclaving and a pH of from about 6.5 to about 7.7 after autoclaving.
8. The process of claim 7 , wherein said at least one carboxyl-containing vinylic monomer is acrylic acid, methacrylic acid, ethylacrylic acid, 2-(meth)acrylamidoglycolic acid, and combinations thereof.
9. The process of claim 7 , wherein the polyanionic polymer is polyacrylic acid, polymethacrylic acid, poly(ethylacrylic acid), poly(acrylic acid-co-methacrylic acid), poly[ethylacrylic acid-co-(meth)acrylic acid], poly(N,N-2-acrylamidoglycolic acid), poly[(meth)acrylic acid-co-acrylamide], poly[(meth)acrylic acid-co-vinylpyrrolidone], poly[ethylacrylic acid-co-acrylamide], poly[ethylacrylic acid-co-vinylpyrrolidone], poly[(meth)acrylic acid-co-vinylacetate], poly[ethylacrylic acid-co-vinylacetate], or combinations thereof.
10. The process of claim 7 , wherein the polyanionic polymer is a graft polymer which is grafted onto the inner layer or the lens bulk material, wherein the graft polymer comprises repeating units of at least one carboxyl-containing vinylic monomer which is acrylic acid, methacrylic acid, ethylacrylic acid, 2-(meth)acrylamidoglycolic acid, and combinations thereof.
11. The process of claim 7 , wherein the lens bulk material is a silicone hydrogel material, wherein the silicone hydrogel bulk material comprises: (1) repeating units of at least one polysiloxane vinylic monomer; (2) repeating units of at least one hydrophilic vinylic monomer; (3) repeating units of at least one polysiloxane vinylic crosslinker; (4) repeating units of at least one hydrophilic N-vinyl amide monomer; (5) repeating units of at least one polycarbosiloxane vinylic monomer; (6) repeating units of at least one polycarbosiloxane vinylic crosslinker; (7) repeating units of at least one silicone-containing vinylic monomer having a bis(trialkylsilyloxy)alkylsilyl or tris(trialkylsilyloxy)silyl group; (8) repeating units of one or more blending vinylic monomers; (9) repeating units of one or more non-silicone vinylic crosslinking agents; or (10) combinations thereof.
12. The process of claim 7 , wherein the lens bulk material is a non-silicone hydrogel material, wherein the non-silicon hydrogel material comprises at least 50% by mole of repeating units of at least one hydroxyl-containing vinylic monomer.
13. A process for producing contact lenses, comprising the steps of:
(a) obtaining a contact lens precursor which is a coated contact lens and has a first polyquaternium-1 uptake (“PU o ”), wherein the coated contact lens comprises a lens bulk material completely covered with at least one layer of a polyanionic polymer, wherein the polyanionic polymer comprises at least 60% by mole of repeating units of at least one carboxyl-containing vinylic monomer; and
(b) heating the contact lens precursor in an aqueous solution in the presence of at least one polyaziridine to and at a temperature from about 30° C. to about 140° C. for a period of time sufficient to obtain the contact lens having a second polyquaternium-1 uptake (“PU pz ”), wherein the polyaziridine having a number average molecular weight of about 2000 Dalton or less and at least two aziridine groups each of which is a mono-valent radical of formula
in which R1 is hydrogen, methyl or ethyl, wherein (PU o -PU pz )/PU o is at least 60%.
14. The process of claim 13 , wherein said at least one polyaziridine is selected from a group consisting of trimethylolpropane tris(2-methyl-1-aziridinepropionate), pentaerythritol tris[3-(1-aziridinyl)propionate], trimethylolpropane tris(3-aziridinopropionate), a Michael reaction product of a vinylic crosslinker having at least three (meth)acryloyl groups and 2-methylaziridine, a Michael reaction product of a vinylic crosslinker having at least three (meth)acryloyl groups and aziridine, or a combination thereof.
15. The process of claim 14 , wherein the aqueous solution comprises two polyaziridines, a first polyaziridine having at least two aziridine groups of
and a second polyaziridine having at least two aziridine groups of
and at least one hydrophilic moiety selected from the group consisting of —OH, —[OC 2 H 4 O] n1 —, —CONHR 1 , —CONR 1 —, and combinations thereof, wherein n1 is an integer of 1 to 10 and R 1 is hydrogen, methyl or ethyl.
16. The process of claim 15 , wherein the aqueous solution comprises from about 0.01% to about 2.5% by weight of said at least one polyaziridine.
17. The process of claim 16 , wherein the aqueous solution is a lens packaging solution, wherein the step of heating is performed by autoclaving the contact lens precursor immersed in the lens packaging solution in a sealed lens package at a temperature of from about 115° C. to about 125° C. for approximately 20-90 minutes.
18. The process of claim 17 , wherein the lens packaging solution further comprises a partially hydrolyzed polyvinyl alcohol having a hydrolysis degree of hydrolysis of from about 80% to about 98%.
19. The process of claim 17 , wherein the lens packaging solution has a pH of from about 7.0 to about 9.0 before autoclaving and a pH of from about 6.5 to about 7.7 after autoclaving.
20. The process of claim 19 , wherein said at least one carboxyl-containing vinylic monomer is acrylic acid, methacrylic acid, ethylacrylic acid, 2-(meth)acrylamidoglycolic acid, and combinations thereof.
21. The process of claim 19 , wherein the polyanionic polymer is polyacrylic acid, polymethacrylic acid, poly(ethylacrylic acid), poly(acrylic acid-co-methacrylic acid), poly[ethylacrylic acid-co-(meth)acrylic acid], poly(N,N-2-acrylamidoglycolic acid), poly[(meth)acrylic acid-co-acrylamide], poly[(meth)acrylic acid-co-vinylpyrrolidone], poly[ethylacrylic acid-co-acrylamide], poly[ethylacrylic acid-co-vinylpyrrolidone], poly[(meth)acrylic acid-co-vinylacetate], poly[ethylacrylic acid-co-vinylacetate], or combinations thereof.
22. The process of claim 19 , wherein the polyanionic polymer is a graft polymer which is grafted onto the inner layer or the lens bulk material, wherein the graft polymer comprises repeating units of at least one carboxyl-containing vinylic monomer which is acrylic acid, methacrylic acid, ethylacrylic acid, 2-(meth)acrylamidoglycolic acid, and combinations thereof.
23. The process of claim 19 , wherein the lens bulk material is a silicone hydrogel material, wherein the silicone hydrogel bulk material comprises: (1) repeating units of at least one polysiloxane vinylic monomer; (2) repeating units of at least one hydrophilic vinylic monomer; (3) repeating units of at least one polysiloxane vinylic crosslinker; (4) repeating units of at least one hydrophilic N-vinyl amide monomer; (5) repeating units of at least one polycarbosiloxane vinylic monomer; (6) repeating units of at least one polycarbosiloxane vinylic crosslinker; (7) repeating units of at least one silicone-containing vinylic monomer having a bis(trialkylsilyloxy)alkylsilyl or tris(trialkylsilyloxy)silyl group; (8) repeating units of one or more blending vinylic monomers; (9) repeating units of one or more non-silicone vinylic crosslinking agents; or (10) combinations thereof.